(2,4,6-Trichlorophenyl)hydrazine → 5-Cyano-6-methyl-1-(2,4,6-trichloroanilino)-2,4-pyrimidinedione

HRID 648162

Reaktionsgleichung

Reaktionsgleichung von HRID 648162
ClC1C=C(Cl)C=C(Cl)C=1NN.[C:12]([C:14](=[C:23]([CH3:35])[NH:24][NH:25][C:26]1[C:31]([Cl:32])=[CH:30][C:29]([Cl:33])=[CH:28][C:27]=1[Cl:34])[C:15]([NH:17][C:18](OCC)=[O:19])=[O:16])#[N:13]>>[C:12]([C:14]1[C:15](=[O:16])[NH:17][C:18](=[O:19])[N:24]([NH:25][C:26]2[C:31]([Cl:32])=[CH:30][C:29]([Cl:33])=[CH:28][C:27]=2[Cl:34])[C:23]=1[CH3:35])#[N:13]

Komponenten

3

Edukt 2

HCID 79234(2,4,6-Trichlorophenyl)hydrazineHCID 70513266alpha-cyano-beta-methyl-beta-(2,4,6-trichlorophenylhydrazino)-N-ethoxycarbonylacrylamide

Produkt 1

HCID 132322555-Cyano-6-methyl-1-(2,4,6-trichloroanilino)-2,4-pyrimidinedione

Versuchsvorschrift

Following the method of Example 1, N-ethoxycarbonylcyanoacetamide is heated with triethyl orthoacetate and acetic anhydride to give α-cyano-β-ethoxy-β-methyl-N-ethoxycarbonylacrylamide, which in turn is reacted with 2,4,6-trichlorophenylhydrazine. The resulting compound α-cyano-β-methyl-β-(2,4,6-trichlorophenylhydrazino)-N-ethoxycarbonylacrylamide (m.p.=183°-184°) is cyclized, yielding 5-cyano-6-methyl-1-(2,4,6-trichloroanilino)-2,4-pyrimidinedione, m.p.=>305°.

Quellen und Nachweise

ORD-Eintrag
ord-aebfeb5fb5064674a31c808ff9acdc9b
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04411839

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